Chicago is a great city. I don't dislike anything about it really. Unlike New York and Los Angeles which I have a love/hate relationship with I find Chicago to be extremely likable but I'm not sure I'd ever date her. She makes great food. She's warm to cuddle up with. I'd go see a movie with Chicago. I'd introduce Chicago to my mother.
Living in New York helps you to realize that other cities are actually quite wonderful. They aren't nearly as daunting to get in and out of. When you visit Chicago, as I am, and your friends complain about the traffic you can lean back as if to say, this level of traffic is down right enjoyable.
I'll miss New York when I leave. And I know one day I'll leave. But I'll never regret leaving and I'll never stare blankly at my new city wishing she were New York.